Methane, dichloromethoxy- → HCID 14348592, compound

HRID 980757Notes

Reaction equation

HRID 980757 reaction equation
[CH3:1][O:2]C(Cl)Cl.[CH3:6][C:7]1[CH:8]=[C:9]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:10]=[C:11]([CH3:15])[C:12]=1[O:13][CH3:14]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:6][C:7]1[C:8]([CH:1]=[O:2])=[C:9]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:10]=[C:11]([CH3:15])[C:12]=1[O:13][CH3:14]

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 14348591HCID 14348591, compound

Product 1

HCID 14348592HCID 14348592, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Dichloromethyl methyl ether (5.3 g equiv) was added slowly to a well stirred mixture of methyl 4-(3,5-dimethyl-4-methoxyphenyl)butyrate (9.75 g) and titanium tetrachloride (31 g equiv) in dichloromethane (200 ml) at 0°-5° C. The mixture was stirred for 1 hr at 5° C. and at room temperature for 2 hrs. The mixture was poured onto ice-water which was then extracted with dichloromethane. The dried (MgSO4) organic fraction was evaporated to give methyl 4-(3,5-dimethyl-2-formyl-4-methoxyphenyl)butyrate as a pale yellow oil. Pmr spectrum (CDCl3 ; δ in ppm): 1.69-2.98 (6H,m); 2.31 (3H,s); 2.52 (3H,s); 3.67 (3H,s); 3.69 (3H,s); 6.91 (1H,s); 10.50 (1H,s).

Workup

  1. stirringThe mixture was stirred for 1 hr at 5° C. and at room temperature for 2 hrs
  2. additionThe mixture was poured onto ice-water which
  3. extractionwas then extracted with dichloromethane
  4. dry with materialThe dried (MgSO4) organic fraction
  5. customwas evaporated

Sources & evidence

ORD record
ord-ac55a568028847c084235b59a6799df0
Source dataset
uspto-grants-1987_01
Patent number
US04639267

Reaction notes

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